Love, Dean
by massivefaceperson
Summary: A story completely based off of Love, Rosie. Dean and Castiel grew up together. They go through years of up's and downs. When will they ever get together?
1. Chapter 1

_**This story is heavily based on Love, Rosie. I came up with the idea to write it after finding Love, Rosie the movie on Amazon Prime. The characters however belong to the writer of SPN.**_

 **Chapter 1: Start at The Beginning**

Dean looked the big venue filled with pastel colors and flowers. _Breathe_ , He echoed to himself. _How did he get here?_ He wondered as his gaze flittered across people and then toward the happy couple. _Meg and Castiel._

Cas, his best friend. On top of that he had to remind himself, _You're the best man. You have to give a speech as you let the love of your life, your best friend, start a life with someone else. Don't panic, Just start at the beginning. Tell them about how you first met._

He could remember the small playground outside of Lawrence Elementary.

He remembers hanging on the edge of the slide about to fall to the ground when a little boy with bright blue eyes and messy hair raised him from the edge of the slide.

"Hi, I'm Castiel." The little boy said.

Dean had replied with, "You've got a weird name."

They smiled at each other and decided to be best friends. From then on the two were inseparable.

Dean could remember all the times they shared notes and call and whispered silly secrets to each other. Or maybe how they always got in trouble by their kindergarten teacher, Zachariah for giggling during class.

Or also all the days he begged his mom and dad to let him run over to Cas's house that was only 3 houses down the street.

Dean remembered all the times they shared all their dreams of travel and escaping the little town of Lawrence.

Castiel even told Dean his weirdest dreams about the angels.

"You know how my mom talks about angels?" Little 7-year-old Castiel asked Dean.

"Uh-huh." Dean smiled along listening intently to Cas as they sat in their pillow fort listening to music on his cassette player.

"Well I keep having more about these angels." Castiel told Dean.

"Well what happened in the last one?" He asked him.

"I was an angel, I had to save you from hell because you were a 'righteous man '. I don't really know what that is but it has to be good right?" Cas asked as he gave Dean a big goofy smile and they broke off into laughs.

Dean thought about telling them about that. _No,_ He thought to himself. _Keep that as our little promise._

Dean could remember everything. The memories played so freshly as he tried to figure out what to say when the love of your life was getting married.

Suddenly he was snapped back to reality by Sam, his younger brother, tapping a glass, signaling him to start his speech. _Tell them this is the happiest day of your life,_ He thought as he stood up for his speech. He cleared his throat signaling for attention as everyone sat down.

"For those I haven't met, Hi, I'm Dean. This has to be one of the happiest days of my life." It was an ironic statement really, when in total he has cried 3 times today.

12 years earlier

The bright lights and music blared loudly at the college party. Dean forced Cas to be here at this college party Lisa had invited him to. He tried to insist that he didn't want to go out and get hammered but Dean replied with, "There is no way in hell, you will not have fun tonight!" Dean's 18th has already past at least a year ago but he had somehow felt it was his right to Castiel hammered on his birthday.

Cas sat on a stool near the bar in the kitchen of the house. Dean had been gone for 5 minutes and trying to get drinks and he was starting to get worried.

He looked around at all the co-eds drinking and dancing as _Crazy in Love_ played in the background.

Finally, Dean appeared but looked more drunk then when he left.

"Dean, sit down you look like your about to pass out." Cas got off the stool and gestured for Dean to sit. He shook his head and stood on one of the legs of the stool balancing himself on the bar.

"Drink this!" Dean slurred as he handed Cas another tequila slammer to go along with his.

"Dean I don't think that's a good idea." Cas tried to shout over the music. Dean douched the shot and almost lost his balance on the bar and decided to grab onto Cas's shoulders instead.

"Come on! Let loose it's your birthday!" Dean whispered in Cas' ear. It was obvious he was beyond plastered.

Dean pulled away from Cas's ear and looked him straight and the eye and kissed him.

Castiel was shocked as he wrapped his arms around Dean's waist trying to deepen the kiss.

Dean pulled away for breath and looked into Cas's eyes.

The moment was completely perfect. Cas smiled and tried to go in for another kiss but at that exact moment Dean's balance slipped as the stool went under him and he fell flat on the floor, knocked unconscious.

Sunlight shone through Dean's window as he woke up in his bed with little recollection of the night before. He remembered the party, the drinks and then blacking out.

He hears his annoying 14-year-old brother Sam open the door as Castiel step through to talk to his mom.

He can hear them talk even though he's all the way upstairs.

"It was all my fault, Mrs. Winchester, I'm sorry I convinced Dean to go to the party." Cas says in his gravelly voice.

He could hear a pause and then his mother's voice, "I would believe you Cas but I know my own son. If you carry on like this, I don't know how this will affect that doctorate you want."

Dean then walks halfway down the stairs to see his mom and Cas talking. "Why are you guys so loud?"

He asks as he's wrapped up in his comforter. He squints his eyes more to see his mother frowning and Cas looking up at him apologetically with his blue eyes.

He then leads Cas up the stairs and flops on his bed.

"Listen, Cas, Buddy I'm sorry for last night." He mutters as hides from the sunlight streaming through his window. "No, no don't apologize It wasn't that bad." Cas offers up.

"Dad is pissed and Sam thinks it's funny." He groans as he turns to face Cas who standing near the door smiling. Cas walks near the bed and flops down next to Dean. "It won't be that bad." Cas promises as he laughs at Deans bitch face.

"It was terrible; I wish it never happened." Dean groans as he looks at Cas. Cas looks worried as he tries to decipher if Dean hated the kiss, which in his opinion was the best part. "Which part was bad?" Cas asks hopefully sitting up a little in the bed.

"All of it was terrible, Let's just forget it all happened." Dean tells Cas as he hides under the blankets. Cas feels ashamed and disappointed in himself for hoping for more. Of course Dean doesn't like him it was a drunken mistake that he can forget about. But Cas couldn't.

The way Dean's lips moved against his own was some type of magic. But he had to forget. For the sake of their friendship.

At that moment Sam barged in yelling, "Dean had to have his stomach pumped!" As he laughed at his brother who threw a shoe at him as Sam ran away laughing.

Dean then curled under the blankets more and asked Cas, "How did we get home from the hospital?" Neither of them had a car and had ridden to the party with Lisa.

Cas gave guilty look and said, "My mom picked us up." Dean gave him a mean stare and groaned.

"They needed a parent's name so I gave them mine. They think you're a terrible influence on me anyway." Cas smiled apologetically as Dean sat up rubbing his eyes.

"Well I am." Dean smiled brightly. "Well now I have to spend all my Saturday's in the library helping out." He said as he looked at Dean. Dean laughed and cupped Cas's shoulder, "Good Luck."

"Well it could be worse." Cas replied with a smile, "Meg has a part time job there."

Dean looked at him, "Cas, Meg is a lost cause, she's out of your league. Hell even I want to sleep with her."

Cas looked hopefully up at Dean and said, "Well at least I can try." Dean laughed as he flopped back into the comforter.

It was a normal summer evening as Cas, Dean and some of their other friends had decided to take a trip down to the lake. Like normal, Dean and Cas played around and Dean even carried Cas on his back.

They separated as Lisa began to flirt with Dean while he was talking to Jo. Lisa led him away to whisper some secret things in his ear. Cas saw this from a distance and started to get a little jealous. _Stop it. You are not dating him. The kiss meant nothing. You've got bigger things to focus on,_ He thought as his gaze flittered over to Meg who across the little bonfire they set up winked at him.

A little later Dean and Cas found their own spot along the fire and talked about the day's events.

"Lisa? Really? She's such a bimbo." Cas scoffed while looking at her from across Dean's shoulder. _"_ She asked me to prom." Dean smiled as he whispered it to Cas. He stuttered nervously hoping that Dean wasn't going to blow off them going together for Lisa.

"What did you say?" He asked with a fake smile.

"Obviously, No, I mean we are going together right?" Cas smiled at his response about to respond, when he saw Meg's milky legs walk up and her appear in front of him.

"I missed you in the library today Clarence." She smiled sweetly. Cas tried to focus on responding but instead stuttered as he saw the small skirt he was wearing and low cut shirt.

"I-I-Uh, Yeah- I umm I was busy umm..." Cas lost the words as she stood above him smiling.

"Don't be a stranger." She leaned down and whispered in his ear as she walked away.

"Uh, I-I yeah, I'll see you there!" He called back as she walked away to rejoin her friends.

Dean gave him a bitch face and laughed.

"Clarence?" He asked as he looked to her then back at Cas, jealousy seeping through his words.

"It's the nickname she gave me, you know the angel," Castiel stated factually.

"Yeah, Yeah I know but that was pathetic." Dean scoffed.

"Huh? I thought there was obvious signs of attraction there." He looked confused.

"Dude, you were stuttering all over the place." Dean gave a frown as he looked down at the grass they sat on. Dean felt kind of jealous but that didn't mean anything. Right?

"Do you have any tips on how she could like me?" Castiel asks with certainty looking staraight into Dean's green eyes.

"Well maybe if you weren't a virgin." Cas lowered his head in shame.

"But maybe we can work with that, act cool around her, also make her feel like you saw something different in her. Then maybe she'll bang you." Cas frowned at Dean's answer.

"Why is it always about sex?" He asked.

"Well isn't that what this whole 'Bad girl Meg' Thing is about?" Dean asked.

"Maybe." Cas replied looking out onto the water. Really he hoped Meg might be some sort of distraction from Dean.

"She wants to go to the dance with me."

Dean looked at him in surprise then looked down and replied, "Then take her if it means so much."

"Are you sure you're okay with this?" Castiel asked because Dean looked a little upset.

He just smiled at Cas and jabbed his finger at Lisa. "Well I do have Lisa to go with."

Cas smiled a bit as they both kept this silent little agreement that they'd go with others.


	2. Chapter 2

**_This chapter is very long and al lot of stuff happens so i hope you enjoy!_**

 _The next day in class_

Dean stared bored at the screen in front of him in his information technology class. He heard Cas whispering his name from three rows over. He looked up to see Cas's gummy smile as he pointed toward the screen. He looked toward the chat page.

 _Impala67: your face annoys me_

 _Assbutt: I've got news!_

 _Impala67: So why did you interrupt my steady concentrated studying?_

 _Assbutt: you were not studying._

 _Impala67: Yes, I was._

 _Assbutt: Dean, you looked bored to death, I know you were not studying._

 _Impala67: Fine whatever. What's the news?_

 _Assbutt: Virgin Boy in no longer._

Dean looked at message in shock.

 _Assbutt: Dean? Are you still there?_

 _Impala67: So who was the unlucky girl?_

 _Assbutt: Meg._

"Shit." Dean curses rather loudly in the near silent classroom. The teacher, Michael look disapprovingly at Dean, "To the principal office. I'm sure you know the way."

Castiel stands up quickly looking flustered and defending dean by saying, "No, it was my fault I'm sorry, I had something I needed to tell Dean." He pleads the teacher with his eyes.

"Yes I see that congratulations, Castiel." The teacher pulls up the chat screen to the board in front of the room. The students clap for Cas as Dean leaves for the principal's office.

* * *

 _The dance_

Castiel ran over to Dean's house in his suit holding his tie. He knocked and as Dean opened the door he looked stunning his suit with the green tie to match his eyes. "I know we aren't supposed to be talking but can you at least help me with my tie?" Cas gave Dean puppy eyes he knew he couldn't resist. Dean dragged him upstairs as he last minute worked on his hair and fixed Cas's tie.

"If I knew any better I would think you were in love with me." Cas said to Dean with a smirk.

"Castiel Jimmy Novak, you will always be known as the weird kid that had an obsession with bees in the third grade." He smiled as he said this.

"Leave them alone! They are majestic creatures!" Castiel spouted in defense as Dean laughed.

"I know friendships like ours can get a little complicated, I just wanted to make sure we were in the clear." Cas said as he adjusted his tie and looked toward Dean.

"I'm always here if you need to talk." Dean said as he looked at Cas.

"what do you think, Sex hair or Normal hair?" Cas asked sincerely as he kept moving his hair in-between the two.

Dean stuttered to respond, "Well, umm, I-I-," He couldn't find the words to piece it together finally he found something, "It depends is it for dancing or for- "Dean trailed off on his words nervously.

Castiel moved really close to him messed with his tie as he whispered in his ear, "Who knows?" and smiled as he walked outside to the car.

* * *

No matter how pissed John Winchester was at Dean, he was gracious enough to let him borrow his 1967 black Impala to go to the prom or as Dean liked to call it, 'Baby.'

They rode up in style and as soon as they pulled up Meg had spotted Castiel. She ran up to the car and pulled him out of it. "So glad to see you Clarence."

She smiled and kissed him on the cheek. "Adios, Cowboy." Meg waved to Dean as she pulled Cas away. "Bitch." Dean replied bitterly as tried to find a place to park.

* * *

The loud music played rapidly as Castiel had Meg grinding seductively on him. On the other side of the dancefloor Dean was smiling widely as him and Lisa were having a good time.

Castiel looked and saw Dean smiling and caught his eye as he pretended he wasn't looking for him although constantly he looked Dean's way.

Dean tried to distract himself with Lisa when really he kept trying to catch Cas's eye. But Cas's was too distracted by Meg and eventually Dean gave up when they started making out on the dancefloor.

* * *

Dean decided to go the full 180 and forget about Cas's as Lisa dragged him upstairs to grab a room in the hotel the prom was in.

They sat on the bed in nervous anticipation as Lisa leaned over his shoulder while Dean tried to put the condom on.

He couldn't quite open the packaging for a while but once he did he hurriedly blew it up and bit and tried to put it on.

"You've done this before right?" Lisa asked as she looked unimpressed to Dean who couldn't put the condom on right.

"Yeah. Haven't you?" He was bluffing this was his first time and really he just wanted to brag to Cas about finally losing his V-Card.

"It's a simple as brushing my teeth." She smiled but looked worried as he was still having trouble putting it on.

He finally put It on but accidently didn't leave room and the plastic snapped on him shooting pain thorough him.

"Shit." He cursed trying to adjust.

"Are you sure you've got this?" she asked still not looking convinced.

He smiled under the pain, "Yeah, Yeah I've got it, Fuck, Ouch. Okay quickly."

She quickly settled under the covers as he climbed on top of her.

He groaned as he finally settled and started. He buried his face in her neck trying to hold on but it was too much. He tried to focus but somehow his thoughts drifted Castiel. She quickly finished as she moaned louder than a firetruck.

"So that was it for you?" He asked somehow afraid he did it wrong.

She looked up at him, "Yeah that was great but you can keep going." He just shrugged and kept going but did not feel aroused by anything that happened with her. In the end he had to think of Castiel to finish. He finally pulled out. She curled into his side as he tried to catch his breath. _Why did I think of my best friend while having sex? God what is wrong with me._ His thoughts were interrupted by Lisa.

"Where is it?" She asked

He looked around, "What?"

"The condom, where is it?" He started to panic as she searched around the bed.

"I don't know where it is." He replied a slight edge to his voice.

She ran to the bathroom, "Oh shit, It's still inside me!" She freaked and ran into the bathroom as Dean gathered up his clothes and called the one person he could rely on.

* * *

Castiel smiled as he saw Meg dancing as he rested. Suddenly his phone rung. Dean's name appeared on screen.

"Dean what's wrong? I was just on my way out." He struggled to hear him over the music.

"Listen Cas, meet me outside near the impala, we have to leave now." Dean's voice was laced with panic but Cas couldn't focus by the way Meg was grinding on him.

Dean was leading a panicked Half Naked Lisa down to lobby. They hopped in the elevator to reach the ground floor while he was still on the phone with Cas.

"Huh? Dean I still can't hear you." Cas yelled into the phone.

Dean and Lisa piled into the elevator that was already occupied by a man in a suit who had a brief case.

"Cas please just meet me outside." He said a little louder so Cas could hear.

"Why, What's wrong dean?" Cas yelled the question into the phone.

"Dammit Cas, a condom got stuck in Lisa's vagina while we were having sex! She can't find it so now we have to take her to the fucking hospital!" Dean yelled into the phone causing the man in the elevator and Lisa to give him strange looks.

The elevator opened at that moment to Cas who said, "That's way more info then I needed."

* * *

After the hospital visit, Dean and Cas drove home alone after dropping Lisa off.

"That was probably the most embarrassing moment in my life." Dean sighed as the pulled up to his house.

They both laughed recalling the incident that happened so recently.

They looked each other in the eyes in comfortable silence.

"You know what, let's get out of here." Cas told Dean.

"What do you mean?" He asked.

"We've always talked about leaving Lawrence we'll let's go. When we apply for college we should both choose the same one. Preferably somewhere far from here." He said as he looked into Dean's green eyes.

"What about Boston?" Dean asked Castiel.

Cas smiled as replied, "We'll get our own apartment and share while we in school. It'll be fun."

Dean smiled back. "We've always wanted to this place is a dead end."

"Yeah. My dad said I should spring for Harvard since I wanted to be a doctor and Boston College does have a business major. You could train to build that little bed and breakfast motel I know you've dreamed about."

Dean smiled

* * *

The next day Dean pitched the idea to his mom and dad.

"You can't! Who will take care of you? What will you do all the way in Boston?'

"Mom, I know how to take care of myself and there I'll be with Cas." He smiled pleadingly trying to convince his mom.

"Talk to him John!" Mary pleaded.

* * *

They sat in comfortable silence as John drove Dean to work with him so they could talk.

"You know son, my grandfather always used to tell me to be realistic. That's how I ended up here being a mechanic."

Dean nodded as his father continued talking.

"Well he always killed my dreams of becoming a car collector like I really wanted and well, I don't want the same for you."

He smiled as his dad went on.

"I don't agree with what you want, personally I think it's weird but if it's what you want don't let me and your mother stop you." He smiled at his son as they pulled up to bobby's shop.

"Alright now get your ass out there and help those customers." Dean's dad barked.

"Yes sir." He agreed as he hopped out of the impala with a smile.

* * *

Dean ran downstairs as soon as he saw the mailman.

He rifled through the letters and finally there it was.

Excited as he tore it open.

 _Congratulations! You have been accepted into Boston University!_

He smiled as he sprinted down to Cas's house.

He knocked as he impatiently waited for Cas to answer.

Instead he came face to face with his little red headed sister Anna.

"Hi, Is Cas here?" He asked hurriedly so excited about the news.

"He's a little tied up right now." She said with a disgusted face. He heard noises upstairs but ignored it.

"It's okay, I can come back." He said.

"They'll be down in about three minutes." She said with a strained face. The weird noises upstairs continued as he followed her to the living room.

"Do you want Tea, Water, Lemonade?" She asked politely.

"Yes, Lemonade would be nice. Thanks." He smiled as she went to grab it for him.

He waited tapping the letter in his hand and sipping the Lemonade carefully.

The 13-year-old next to him idly texted and ignored her surroundings.

He smiled but started listening into the noises that sounded like moans?

He heard Meg's voice saying, "Yes! Yes! Angel Yes!"

"Are they?" He looked at the teenager.

"Yep." She replied nonchalantly

"Is that-?"

"Meg." She finished his sentence.

"So when you said he was-?"

"Tied up." She answered.

"You actually meant tied up?" He thought of that mental image and didn't know if he was scared or pleased.

"Yes." She answered.

"I should uh… go umm…" He nervously tried to leave.

The moans upstairs got louder.

"Any second now," She said as the moans increased.

He could hear the moans so clearly as Anna _literally_ repeated them what meg said word for word,

" _Oh, Clarence, where did you learn to do that?"_

"I think I'm going to be sick, "he said as he frantically searched for a trash can, he ended up throwing up in the Novak's kitchen sink as Meg's moans continued.

* * *

That night, Lisa had called him and told him to meet him at this weird pharmacy so she can buy pregnancy tests. With all the Cas stuff still replaying in his mind, he freaked at the thought.

 _I might have gotten a girl pregnant by getting a condom stuck in her._

He walked into the weird pharmacy that was playing loud rock and roll music. There were green lights everywhere and a ton of weird products he was sure did not come in a normal pharmacy.

He nervous walked up to the counter as he heard glass break and a loud voice yell, "Fuck!"

He rang the bell at the front as the same voice yelled, "Coming!"

Finally, the person appeared as it was a tiny red heard with bangs. Her name tag read, _Charlie_ and she looked really nervous.

"Okay look my parents own the place and this is my first time actually working here and I'm so sorry if I'm babbling it's just I'm nervous because I just broke a bottle with some green liquid back there and oh my god." She pushed her bangs out of her face and breathed in.

"I'm really sorry about that, how can I help you?" She asked again calmer this time.

"I need umm- Pregnancy test; this girl was supposed to meet me here uh…" He trailed off feeling weird telling someone this.

"Oh okay that's fine just pay for them and you're all set." She smiled as he handed her money and she bagged the tests.

"So how did it happen?" She asked

"What?" He asked confused.

"How'd you get her pregnant?"

"Umm- "It was awkward to tell a complete stranger an embarrassing story.

"It's fine, I once got a butt plug stuck up my girlfriend's butt so how bad can it be?" She smiled

He uneasily spilled, "A condom got lost up her vagina and now she missed a period."

Charlie laughed and grabbed his shoulder.

"See it wasn't that bad."

He decided him and Charlie were friends.

Lisa took the test in the bathroom at the pharmacy and both came positive.

He dropped her off shortly after having a comforting hug from Charlie, his new friend.

Obviously she didn't want to give the kid up so now it was building a life.

As soon as he got home he logged onto the chat sight to get some comfort from Castiel.

 _Impala67: Cas are you there? Can we meet?_

 _Assbutt: I would love to but Meg's parents are taking us out to a fancy restaurant. How cool is that?_

 _Impala67: FUCK THAT BROWN HAIRED BITCH. CAS, LISA IS PREGNANT PLEASE I DON'T KNOW WHAT TO DO. - unsent_

Dean thought about sending that message but instead opted out.

 _Impala67: okay. Have fun._

Dean then sat in his room alone hiding in the comforter as tears streamed down his face.

* * *

 ** _The next day_**

Dean sat looking down at the table in the small cafe messing with the napkins when and undone rushed Castiel appeared.

"Okay, I'm sorry!" He said as he sat down. He looked insane, with his hair fluffed up all the way and his sweater weirdly buttoned like he was in a hurry.

Castiel held his letter in front of his face with hopeful eyes that made Dean smile a bit.

"I've got news!" He said excitedly.

"Me too." Dean said a little bit sad.

"Okay open it first!" He handed Dean the letter to open as he carefully read it.

"Scholarship to Harvard." He read off the paper in disbelief. His eyes rimmed with tears.

"Congratulations Cas, That's unbelievable." He gave him a sad smile.

"Have you heard back from Boston college yet?" Cas asked hopefully.

This was the time to tell Cas that he had to stay because of Lisa. But looking in those big blues, he couldn't bring himself to do it.

"No, not yet." He said looking down at the table.

Cas looked concerned but reassured him, "You'll get in."

"What about Meg? Have you told her?" He asked.

Cas looked kind of sad for a moment then shook it off, "She'll be fine. But She's got this thing about my hair," He ruffled his hair as he continued, "She yanks it and pulls this funny face during sex like,"

Cas then opened his mouth into a weird face making Dean laugh while more tears brimmed his eyes.

He wished he could go to Boston and be with Cas.

He wished he could be happy like Cas.

"Don't worry we're on our way to Boston!" He smiled.

Dean just looked on with a sad smile as Cas continued.

"I have an apartment for us that's set up there, in a few days I'm going to go look." He brightly looked at Dean who nodded.

"That's great. Have fun." He replied

"Aren't you coming? My flights in three days which means you need to book your too" Castiel asked hopefully.

"Yeah, I've got some stuff to sort first but I'll be there." Dean lied and Castiel's smile after that broke his heart even more—

* * *

 _ **A few days later**_

"Don't get murdered by terrorists." Dean commanded while walking Castiel to his terminal in the aiport

"Okay." He laughed as they walked

"Or lose cabin pressure and fall out of the sky," Dean rambled on.

"Dean…" Castiel started but Dean interrupted him once more, "Also don't fly into a flock of birds."

They stopped walking as Castiel turned around, his huge trench coat moving with him.

"I can delay it if you want me to." Castiel offered.

Dean looked him in the eyes and decided, "No, you're getting on that plane."

Castiel smiled at him and told him to close his eyes. Dean was hesitant at first but did.

Cas took his hand and arranged it to where he was pointing his finger.

Castiel took out a little globe that would go on key chains and spun it. His finger stopped the globe on a continent and when he opened his eyes he saw it.

"North America." He smiled when he saw it.

He remembered this from when they were kids. They would spin this huge globe Cas had in his room and close their eyes as their fingers laid on a place. Then they vowed they'd so their one day. That was their promise to see each other again.

At that moment Dean hugged Cas tightly with tears in his eyes. When they pulled away with their lips so close he wanted to kiss Cas and tell him he loved him and about Lisa.

But they both knew it was wrong as they laid their foreheads against each other's. They pulled away, yet still close as Dean whispered , "Keep in touch Please." Cas nodded as they smiled at each other.

"See you in two weeks Dean." Cas walked away farther and farther then right before he was out of sight turned and waved goodbye to Dean, then was gone.


	3. Chapter 3

"If I told him he wouldn't have left and then I would ruin his whole life too. What's the point?" Dean sighed as he talked to Charlie in the weird pharmacy he had now gotten strangely accustomed to.

"Personally, I would have forced him to stay if he was my girlfriend." Charlie said as she bustled around refilling shelves with liquids and pill bottles.

"No, I couldn't have done that. It would have ruined him and his dreams," Dean muttered as he fielded with the tiny globe Cas left him. Charlie went back around the counter and Dean followed her leaning against the glass. She smiled put her chin in her hands and stared at him.

"Basically you're in love with your best friend, but can't tell him to stay because you got someone chick pregnant that you used to get over him? This is as dramatic as the plot of The Empire Strikes Back." She smirked a bit and asked, "Why don't you just ask her to get rid of it?".

Dean shook his head rang his hand down his face in frustration, "No, I couldn't do that I mean her parents are Catholic. She doesn't really believe in that stuff."

He turned to look at her and sighed, "How did it end up like this? I had it all planned. Move to Boston, Live with Cas, go to school and get my business degree. Maybe eventually he'd fall in love with me and we would buy a small lot to make that bed and breakfast I always wanted."

He smiled at the thought. But that was a distant dream now that felt so far removed now that he looked at the inevitable.

"Yeah and Bilbo thought It would be a small journey outside of the Shire." She sighed as she unloaded more boxes behind the counter.

"Now it's goodbye to Cas, Domestic bliss with Lisa in the stupid town and a steady job as a mechanic." He sighed.

"You should just kill yourself now. I can sort the drugs!" Charlie said happily as she shook a pill bottle she was loading.

Dean chuckled, "Yeah maybe I can ask her to give it up, for adoption. That would be smart. Then I could still move to Boston! Is that even remotely a good idea?"

"Yeah, totally dude." She smiled and gave him a high five.

"I don't even have to tell Cas!" Dean smiled.

"Whoa, dude that's seriously Darth Vader level denial." Charlie said while making a gesture.

"I just thinking It's smart emotional investment." Dean said with a smirk

"Maybe everything Is looking up." He mumbled as he looked down at the globe tilted toward North America.

* * *

From then on, the countdown to Boston started. Lisa had agreed to give up the baby but from then a daily routine had started. He would go over to Lisa's and have dinner then talk to her parents for a bit.

He kept in mind not to get attached to the kid but one eventful day when they went to get an ultrasound that changed everything.

As him and Lisa sat in that room it felt beautiful. He could hear the baby's heartbeat and he laughed as he held Lisa's hand. The baby kicked and titled around making them both smile.

"Do you want a picture?" The nurse asked. Of course Dean couldn't have refused as he walked inside to show the picture to his family.

Sam had stared in amazement at the picture, "So I'm going to be and uncle?" He asked excitedly while flashing Dean one of the brightest smiles.

"Yeah you are." He smiled.

"What's the little angel's name? He looks so adorable!" His mom cooed at the picture.

"It's actually a girl mom." He smiled remembering him and Lisa talking about names.

His dad looked down at the picture and told him, "I know hard this was for you Dean, but you're doing the right thing." Dean smiled as his father clapped him on the back before heading to the garage.

Dean kept the picture tucked in the picture of him and Cas at the beach that one summer. He was determined to make it back to Cas. But it would be a little harder with this baby that was slowly growing on him.

 _ **A few months later….**_

It was 9:30 on a Wednesday night when Dean got a panicked call from Lisa's mother. All he could remember was screaming through the phone as her mother called him while going she was going into Labor. Panicked, He ran and grabbed Dad's keys to the impala without a second thought. He drove faster than he probably should have, cutting of cars and going way over the speed limit. His thoughts were simply focused on the fact that he was about to have a kid.

As he finally pulled into the hospital parking lot, he ran to the nurse's desk looking frantic.

"Is there a Lisa Braeden in any of these rooms?" He asked quickly as he looked around hoping to find her family.

"Sir, I know where she is but I can't let you in when the patients in labor." The nurse said sympathetically.

"Look, I'm the one who got her pregnant, It's my kid in there so come on tell me!" He shouted at the nurse.

She jumped back ran from out the front desk and gestured for him to follow her. She walked fast as Dean jogged to catch up with her. As she showed him the room where her Dad sat outside and then walked away.

He looked up as he saw Dean He gave a sad smile but flinched at the sound of Lisa's screams inside.

"We can't go in so we might as well wait." He told Dean.

Dean nodded and sat down next to him.

"I wanted to hate you for getting her pregnant. I mean I knew my daughter would go out and be with guys but I didn't imagine it would finally happen." Dean looked down in shame as he continued.

"I'm glad it was you though. At least it wasn't one of those others jerks who would have left as soon as she told him." Dean smiled at this and continued to wait.

 _ **6 hours later**_

At 4:30 am on Thursday that Claire Winchester was born Dean was the first to hold her as Lisa had passed out right after. He smiled down at her and her blonde fuzz of hair. Her tiny hands grasped his finger, her whole hand wrapping around his fingertip. He smiled bigger than he ever had. He wondered how he could ever give her up.

Soon enough the nurse had to take her away to take vitals so he left her go but he realized that little bundle of joy was his everything.

 _ **A few days later**_

Dean hadn't heard from Lisa in a few days and was starting to get worried. He had thought at first it was just her adjusting but he wasn't so sure. Then he heard the doorbell ring during dinner with his family. Sam was babbling on about this cute girl named Jess when it happened. His mom ran to open the door when he heard a child crying. "Dean!" His mother called from the door. He walked to the front to see him mother holding Claire. "Mom what is Claire doing here? I thought Lisa had her?" His mother smiled as she handed him a note that read:

 _I couldn't handle anymore. I can't keep her but I can't give her to a random stranger. Please take care of her Dean._

 _Lisa_

Dean wanted to be mad at Lisa for leaving him like this but really he was more glad Claire was with him.

* * *

In the next few days Dean learned some important pointers,

1\. Never take Claire to Job Interviews (A lesson learned as she puked on the guy interviewing him.)

2\. Don't panic at her crying

3 . Always carry baby wipes

4\. Try not to think of Castiel Novak

He hadn't seen or talked to him since he left. He hoped that Cas had forgotten about him but honestly. That would make this whole situation easier. However, he had broken that fourth rule.

It was Sunday and he had gotten accustom to having Claire on him 24/7. He was fine and dandy shopping for baby clothes downtown when suddenly out of nowhere there she was, _Meg._ What was she doing here? Why was she here? What if she told Cas? All these thoughts flooded him as he stood frozen. Then she spotted him.

She started to walk across the street with a curious look but his first instinct was run.

He tried to hide behind the stroller on the sidewalk and move backwards with the stroller but that was equally harder as he was 6'1.

As he kept moving back he could see the alley he was trying to hide in. _Run, Run, Run!_ He was almost there then as he stood up he accidently tripped sending him flying backwards into a rack of clothes. _Shit, she definitely saw me now._

As laid buried in clothes on the cement he wondered _how did I end up like this?_

Then he felt a hand peel the clothes off his face as he saw Meg appear.

"Dean-O?" Meg asked in shock.

"Yeah, hi..." Dean said awkwardly in response. Meg helped him as he stood brushing off dust. He saw Claire's stroller and looked to make sure she was okay.

"Tell me that's not your kid." Meg looked at the baby in disgust. Although Dean loathes her he had to make sure she didn't tell Cas.

"No." He scoffed and chuckled in reply looking down at Claire who softly cooed in her stroller.

"So you're a nanny now?" Meg asked with curious eyes.

"Yeah, it pays really good money." Dean said as he leaned against the stroller casually.

"But I thought you were in Boston with Castiel?" Meg asked with a prying tone. And there was the name he had been avoiding for months. The one person who couldn't know about Claire.

He quickly replied with, "Oh No, I realized children are the only education you need." Dean gave a fake smile as Meg gave him a weird look.

"She is adorable." Meg smiled as she leaned down to touch Claire. At that moment Dean had never been prouder of his little girl as she yanked Meg's hair.

"Get it off! Get it off!" Meg screamed. As soon as Claire let go Dean saw that as their cue to go as he said a quick goodbye and ran off with Claire.

* * *

Dean was folding baby clothes downstairs as Claire slept. Then he heard a knock on the door he walked assuming it was the mailman. But he opened it to something even better.

It was Cas. Dean was so pleased to finally have him here. He missed his chiseled face with the deep blue eyes and chapped lips. He looked older as his hair was cut and combed a bit. But he was still Cas, Dean's best friend.

"Cas, what are you doing here?" He said in shock. Cas felt older by the way he stood like he was so sure of himself. "Just got in and I thought I'd surprise you." Cas said in his normal silky yet rough voice.

"Yeah, let me get my coat and we can-," Dean reached for his normal brown coat but was stopped by Cas.

"No we could stay here. I'll make some tea." Cas smiled as he started to set in to the house. Dean moved aside as Cas put up his jacket.

Suddenly Dean remembered Claire. He ran quickly to the living room to hide the baby clothes and blankets. He moved all the toys and ran to the kitchen to clear out all the baby food and bottles as Cas trailed far behind him.

"So what have you been doing Dean?" Cas asked as he stood farther near the door.

"Oh yeah know the usual. Nice Haircut by the way." Dean bustled about clearing dishes and food in the living room. "Are you okay Dean? You seem a little stressed.

He could hear Castiel move closer into the kitchen, Dean got there first however moving the feeding chair. "Oh no, I'm fine. How's Boston?" Dean called from the sink.

"It's fascinating. I wish you could see it." Cas answered as he stood hear Dean who was cleaning things in the sink.

Dean wasn't looking at Cas as he leaned against the counter, "How do you find these labeled baby bottles they must be hard to find." Cas asked.

"Oh yeah, I was lucky that Mom got mine for Claire-"It was only after he has said her name he realized Cas knew.

 _Cas knew._

He stopped messing with the dishes and looked down at the sink in shame.

"How did you-?" He turned to face Castiel as he asked and saw him holding the baby bottle.

"Meg." He answered putting the bottle on the counter next to him still not matching Dean's gaze.

"I Was-I was going to tell you Cas, I promise." Dean said softly to Cas.

" When?" Castiel asked finally matching Dean's gaze. Dean knew he wanted to tell Cas but at this point couldn't find the words to explain why he didn't say anything sooner.

"I didn't want to hold you back from your dream Cas." Dean whispered it softly in the quiet room.

* * *

Dean wished he could freeze this moment with just him and Cas in his bed with a sleepy adorable Claire.

"My whole life now is Claire. It's has no room for anything else really." Dean whispered it to Cas as he continued to trace small patterns with his finger on Claire's chest.

Cas smiled and then asked, "What happened to Lisa?" He turned his big blue's to Dean as he gave him a worrying gaze.

"She suddenly disappeared leaving this little of bundle of joy on my doorstep. What else could I do but keep her?"

Cas smiled and then quietly asked, "Can I be her godfather?"

Dean flashed him on of the biggest smiles. "I'd love nothing more Cas."

* * *

Before Castiel left they visited the lake. No one was there as they stared out to the small waves while sitting on the grass.

Dean felt near crying as he didn't want Castiel to leave.

"If I didn't tell you I figured we could still keep the dream alive." Dean told him as he looked out the lake hoping Cas wouldn't see his tears.

He looked at Cas and they stared into each other's eyes.

"You know so there was at least one person out there who still saw me as me. Not Dean the weird new dad." He said this as Cas looked at him with concern. Cas looked down a bit and gave a small smile.

Castiel held out his hand as Dean wrapped intertwined their fingers.

"You'll always be just Dean to me." Cas told him as he squeezed his hand and looked out onto the lake.

* * *

When Dean got home he laid Claire on his chest as he spun his globe and closed his eyes and his finger landed on the one place he wanted to be, _Boston._

* * *

Castiel sat in the bar somberly looking down at his lousy beer. After seeing Dean like that he didn't know what to say.

He had loved Dean for so long. All he wanted was for Dean to be happy.

But now Dean had a kid.

Of course that meant any dream Castiel had for them falling in love while they were in Boston together was impossible.

How could he?

Dean looked happy with Claire and if Castiel forced him to be here for his personal needs it would be terrible.

Castiel buried himself in his thoughts when suddenly a shorter yet stout man appeared. He tried to ignore him but it looked like the man was trying to ask him a question.

"So," He yelled above the music trying to grab his attention. Castiel looked briefly at the short man with longish brown hair.

"The last time I saw someone look that depressed they tried to hang themselves." He yelled as he smiled at Castiel.

Castiel gave him a strange look as the man gave him a small smile and introduced himself, "Hi, I'm Gabriel." He said as he reached out a hand for Castiel to shake.

Castiel shook his hand briefly and gave him a polite smile. Before he could pull his hand away Gabriel pulled him in and clasped his hands around Castiel's.

"I've been sent to play fairy godmother," He said as he still held Castiel's hand.

Castiel still feeling very uncomfortable said, "You don't look the part."

Gabriel laughed, let go of his hand and continued, "My sister is driving me crazy, she wants to know if you will buy her a drink."

Going by the appearance of this man Castiel was scared to agree. He took a deep breath in and asked,

"Which one is she?"

Gabriel pointed to a surprisingly attractive young woman with long brown hair and blue eyes and a small sundress.

Castiel gave a bright smile of disbelief.

"The hot girl from class?" He asked.

"Her name is Hannah the bright sunflower in a family of weeds." Gabriel told him as Hannah walked over.

"Hey," She smiled as she leaned over the table he was sitting at.

He smiled back as she told him, "Everybody's been wondering why the cute boy in class always looks so sad." She said while she twirled her hair back and forth.

"I'm sorry." He said with a small smile as he stared at Hannah.

"It's time to realize you're with us now and we might actually be a little fun." She smiled as she leaned closer to him smiling bright.

And of course Castiel couldn't do anything but smile back.

 _ **Please Please review, favorite and follow, i really need to know if people actually like this story or if they just want me to quit writing it.**_


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